ethyl [5-amino-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene]-α-D-gluco-heptofuranuronate | 742077-97-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl [5-amino-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene]-α-D-gluco-heptofuranuronate
• 英文别名: ethyl 5-amino-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-D-gluco-heptofuranuro；(1R,2R,3S,4R)-ethyl-[5-amino-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene]-α-D-gluco-heptofuranuronate；ethyl (3R)-3-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-3-aminopropanoate
• CAS: 742077-97-0
• 化学式: C₁₉H₂₇NO₆
• 分子量: 365.426
• InChiKey: HAOPMNGSBHHCGF-SOVHRIKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  89.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl [5-amino-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene]-α-D-gluco-heptofuranuronate 在 哌啶 、 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 ethyl (5S,8S,11S,14R)-8-benzyl-14-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-1-(9H-fluoren-9-yl)-5-isobutyl-11-(2-(methylthio)ethyl)-3,6,9,12-tetraoxo-2-oxa-4,7,10,13-tetraazahexadecan-16-oate
  参考文献：
  名称：

  Robust Turn Structures in α₃β Cyclic Tetrapeptides Induced and Controlled by Carbo-β³ Amino Acid

  摘要：

  Designing cyclic tetrapeptides (CTPs), which fold into desired structures, is often a challenging task. While it is difficult to synthesize them, they are also prone to adopt multiple conformations. In this paper we report the synthesis and conformational studies of CTP mimics, having nonconstrained alpha(3)beta motif, that exhibit stable beta- and gamma-turn structures. We also demonstrate the transformation of beta-turn to gamma-turn structure in similar CTPs by inverting the chirality of beta carbon in C-linked-carbo-beta(3)-amino acid (Caa) from R to S.

  DOI：

  10.1021/jo2019834
• 作为产物：
  描述：

  (1R,2R,3S,4R)-ethyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]heptfuran-5-enuronate 在 氨 作用下， 以 乙醇 为溶剂， 以60%的产率得到
  参考文献：
  名称：

  D-葡萄糖多种糖基化脲的合成及抗结核作用评价

  摘要：

  通过将胺1,4-共轭加成到糖基化烯酯上，然后将所得糖基β-氨基酯与二异氰酸酯反应，以良好至优异的产率合成了N,N-二取代的糖基化脲。所开发的糖基分子通过广泛的标准光谱分析（包括 NMR（1 H、13 C 和 DEPT）、IR、MS 和元素分析）得到了很好的表征，并筛选了其抗结核分枝杆菌( M. Tb. )的生物活性。 ，其中一些表现出有效的抗结核活性。这些分子的设计考虑了参与分枝杆菌细胞壁聚合物生物合成的众所周知的酶抑制剂，并且可以作为先导分子进一步探索，以成功开发潜在的抗结核候选药物。

  DOI：

  10.1155/2024/8709672

文献信息

• Asymmetric organocatalysis with glycosyl-β-amino acids: direct asymmetric aldol reaction of acetone with aldehydes
  作者：Namrata Dwivedi、Surendra S. Bisht、Rama P. Tripathi

  DOI：10.1016/j.carres.2006.08.007

  日期：2006.11

  Direct asymmetric aldol reaction of acetone with aromatic aldehydes was achieved in good yields and high enantioselectivity using 5-amino-5-deoxy-beta-L-ido-(alpha-D-gluco)-heptofuranuronic acids as a new class of organocatalysts.

  使用5-氨基-5-脱氧-β-L-氨基-（α-D-葡萄糖）-呋喃呋喃糖醛酸作为一类新型的有机催化剂，可实现丙酮与芳族醛的直接不对称醛醇缩合反应，并具有良好的收率和高对映选择性。
• Investigation and folding pattern of l-ido and d-gluco peptides by EASY ROESY NMR and X-ray
  作者：Sachin A. Pawar、Amit M. Jabgunde、Katja Petzold、Glenn E. M. Maguire、Dilip D. Dhavale、Hendrik G. Kruger、Thavendran Govender

  DOI：10.1039/c3ra44542a

  日期：——

  The sugar β-amino acid plays an important role in the formation of well-defined secondary structures of peptides. The combination of change in the functional group, stereocenter on the sugar amino acid and peptide attachment to the glycopeptide revealed important information about their secondary structure. The stereocentre (C5–H) of the sugar β-amino acid in these peptidic diastereomers controls the folding behaviour of these compounds. Conformations of the considered compounds were established by NMR (EASY-ROESY) and compared with the 3D structure obtained from X-ray crystallography.

  糖 β-氨基酸在形成定义明确的肽二级结构中起着重要作用。糖氨基酸上的官能团、立体中心和肽附着在糖肽上的变化相结合，揭示了其二级结构的重要信息。这些肽非对映异构体中β-氨基酸糖的立体中心（C5-H）控制着这些化合物的折叠行为。通过核磁共振（EASY-ROESY）确定了所研究化合物的构象，并与 X 射线晶体学获得的三维结构进行了比较。
• One-Pot Synthesis of Glycosyl-β-azido Ester via Diazotransfer Reaction Toward Access of Glycosyl-β-triazolyl Ester
  作者：Amrita Mishra、Vinod K. Tiwari

  DOI：10.1021/acs.joc.5b00179

  日期：2015.5.15

  A concise and efficacious one-pot protocol for the synthesis of novel glycosyl-beta-azido ester 3 from glycosyl olefinic ester 1 under mild conditions has been devised. The beta-aminoester, formed by the conjugate addition of ammonia on olefinic ester, undergoes a metal-catalyzed diazotransfer reaction to furnish glycosyl-beta-azido ester. The optimized conditions for diazotransfer reaction indicate that imidazole-1-sulphonyl azide and K2CO3 give the best results in the presence of ZnCl2. A diverse range of novel regioselective triazolyl glycoconjugates 6a-u have been achieved in high yields via 1,3-dipolar cycloaddition of compound 3 with various alkynes in the presence of Cul/DIPEA. Structures of all the compounds have been elucidated using IR, NMR, MS, and elemental analysis, and four of them (3a, 3b, 4b, and 6a) have also been characterized by single crystal X-ray diffraction analysis.
• Synthesis of glycosylated β-amino acids as new class of antitubercular agents
  作者：R.P. Tripathi、R. Tripathi、V.K. Tiwari、Laxmi Bala、S Sinha、A. Srivastava、R. Srivastava、B.S. Srivastava

  DOI：10.1016/s0223-5234(02)01398-3

  日期：2002.9

  A series of glycosylated P-amino acids was prepared and evaluated against Mycohacterium tuberculosis, M. avium, M. fortuitum and M. smegmatis. The compounds were designed to mimic the enzyme D-alanine racemase and glycosyl transferase involved in the biosynthesis of essential cell wall peptidoglycan and arabinogalactan. Though most of the compounds exhibited little activity, however, one showed significant activity against all the strains in cell culture and activity was confirmed by BACTEC method. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
• A Versatile Synthesis of Dihydropyrimidinone<i>C</i>‐Nucleosides
  作者：Ram Chandra Mishra、Diksha Katiyar、Neetu Tewari、Rama Pati Tripathi

  DOI：10.1081/ncn-120030712

  日期：2004.12.31

  A versatile synthesis of N-substituted dihydropyrimidinone C-nucleosides (20-29) is described. Glycosyl amino esters (3-9), obtained by reductive alkylation of glycosyl amino esters 1 and 2, on condensation with different isocyanates afforded respective ureido derivatives (10-19) in good to quantitative yields. The latter on cyclative amidation with a combination of DBU/TBAB (tetrabutylammonium bromide)/4Angstrom molecular sieve gave the corresponding nucleosides (20-29) in good yields.